Last updated: September 2026
Every November and December a group of superyachts crosses the Atlantic from the Mediterranean to spend the winter in the Caribbean, and others stay in the islands all year. This countdown ranks the 12 biggest superyachts listed on this site with the Virgin Islands, the Leewards or the Windwards as their winter cruising area, by listed length, with ties broken by beam. It runs from #12, the 150 foot KEFI, to #1, the 218 foot OKTO. After it come ten more Mediterranean yachts, most of them bigger, up to 400 feet, that aren’t listed here but that our brokers can book.
The Caribbean charter season runs from December to April. Rates are weekly, in the currency each listing uses, and exclude expenses such as fuel, food and berthing. Those are paid up front as an advance provisioning allowance (APA), shown below as “plus APA”, commonly 25 to 35% of the charter fee, and a crew gratuity is customary on top.
The 12 biggest superyachts listed for a Caribbean winter
12. KEFI
“A Caribbean Boat All Year”
KEFI is a 150 foot Christensen motor yacht, built in 2005 and refit in 2026. Several boats in this countdown cross the Atlantic each year. KEFI is one of the ones that stay: her listing keeps her in the BVI, the USVI, the Leewards and the Windwards in winter, and in the same waters plus the Bahamas in summer.
She takes 12 guests in 6 cabins with 9 crew. Ask us for her full specification. Rates run from $175,000 per week off-peak, up to $195,000 per week plus APA.
11. JUBILEE
“Summers in Sardinia, Winters in the Islands”
JUBILEE is a 151 foot Pendennis motor yacht from 1999, refit in 2020. She is one of the boats that cross the Atlantic every year: summers in Sicily, Sardinia and the French Riviera, then a winter in the Bahamas, the Leewards, the Windwards and the BVI.
She takes 12 guests with 13 crew. Ask us for her current cabin layout and full specification. Rates run from €180,000 per week off-peak, up to €210,000 per week plus APA.
10. HYPERION
“A 156 Foot Sloop for Six Guests”
HYPERION is a 156 foot Royal Huisman sloop built in 1998 and refit in 2023. She takes only 6 guests, in 3 en-suite cabins: a full-beam primary suite with a king bed and a study, a queen and a twin. She has 8 crew, more crew than guests.
She is a boat for people who want to sail, and the toy list leans that way too: kiteboarding kit, a windsurfer, wakeboards and water skis. She summers in the Balearics and Northern Europe and winters in the Leewards, the Windwards, the USVI and the Bahamas. Her winter rates run from $112,000 per week, rising to $135,000 per week over Thanksgiving, Christmas and New Year. Ask us exactly what the rate includes.
9. ARABELLA
“The One for a Big Group”
ARABELLA is a 157 foot Palmer Johnson sailing yacht from 1983, refit in 2000. She is the outlier on this list. Most superyachts take 12 guests, and ARABELLA is laid out for large groups: her listing describes up to 40 guests in 20 en-suite cabins, 6 VIP staterooms, 2 doubles and 12 twins, each with a porthole, with 6 crew. That makes her a different kind of charter from the rest of this list, so ask us how she operates for a group your size.
She spends summer in New England and winter in the BVI, the USVI, the Leewards and the Windwards. There is a Jacuzzi aft, and she carries a 20 foot RIB, kayaks, paddleboards and two Pico dinghies. Rates run from $125,000 per week off-peak, up to $135,000 per week plus APA.
8. NO BAD IDEAS
“Two Jacuzzis, One at Sea Level”
NO BAD IDEAS is a 160 foot Trinity motor yacht, built in 1999, delivered in 2000 and refit in 2024. She has two Jacuzzis: one on the sun deck and an infinity-style one on the swim platform, right at the water.
The toy list is long: 4 jet skis, 4 SeaBob F5s, an eFoil, an inflatable slide from the sun deck and an inflatable climbing wall, plus a 32 foot Intrepid center console. She takes 12 guests in 6 staterooms, including a full-beam master on the main deck, with 9 crew. She winters in the BVI, the USVI, the Leewards and the Bahamas, and stays in the Bahamas for summer. Rates run from $225,000 per week off-peak, up to $250,000 per week plus APA.
7. TCB
“A 38 Foot Tender With Four Engines”
TCB is a 164 foot Trinity motor yacht from 2008, refit in 2022. Her main tender is a 2021 Scout, 38 feet long with four 350 hp Mercury outboards, and there is a 21 foot inflatable for beach drops.
At the stern there is a beach club, an extended swim platform and an inflatable dock, and the toys include 2 waverunners, 2 SeaBobs and 2 eFoils. Up top there is a deck Jacuzzi and a gym. She sleeps up to 12 guests in 5 cabins; ask us for the exact sleeping layout. She winters across the BVI, the USVI, the Leewards, the Windwards and the Bahamas, and stays in the Bahamas for summer. Rates run from $175,000 per week off-peak, up to $200,000 per week plus APA.
6. SWEET CAROLINE II
“A Butler’s Cabin Near the Master”
SWEET CAROLINE II is a 165 foot Trinity motor yacht built in 2009 and refit in 2021. She sleeps 12 guests in 7 cabins, and one of them is a butler’s cabin near the on-deck master, which her listing suggests for young kids or an extra person.
There is a sun deck Jacuzzi with a bar, a gym with a treadmill and a massage table, and a full-beam dining room. She carries 2 jet skis, 3 SeaBobs and a slide from the top deck. She stays in the BVI, the USVI, the Leewards, the Windwards and the Bahamas all year. Rates run from $199,000 per week plus APA.
5. YCM FIFTY
“A Bannenberg Design With Starlink”
YCM FIFTY is a 165 foot Oceanfast motor yacht from 1989, and her listing credits Jon Bannenberg with both the exterior and interior design. She ties SWEET CAROLINE II at 165 feet and ranks above her on beam, 9.75 meters against 8.53. She has Starlink internet and stabilizers that work at anchor.
On deck there is a Jacuzzi, an exterior bar, a barbecue and an outdoor shower. The toys include 2 jet skis, a SeaBob, waterskis, a wakeboard, paddleboards and a water slide. She sleeps up to 14 guests in 6 cabins. She winters in the BVI, the USVI, the Leewards, the Windwards and the Bahamas, and her listed summer areas include Sicily, Sardinia, the French Riviera, the Balearics, the Bahamas, the Leewards and Tahiti. Rates run from €160,000 per week off-peak, up to €180,000 per week plus APA.
4. SOUTH
“A Sauna, a Steam Room and a 41 Foot Tender”
SOUTH is a 180 foot Heesen motor yacht built in 2012 and refurbished in 2023. She has a beach club, a deck pool, a gym with TechnoGym equipment and a Peloton, a massage room, a sauna and a steam room.
Her 41 foot Valhalla center console works as a day boat, and the toys include 2 WaveRunners, 3 SeaBobs, an eFoil and an inflatable slide with a 21 foot drop. She takes 12 guests in 6 cabins with 14 crew, and spends the winter between the BVI, the Leewards and the Bahamas, and the summer in the Bahamas and the Leewards. Rates run from $320,000 per week off-peak, up to $350,000 per week plus APA.
3. TOP FIVE II
“A Whole Deck for the Owner’s Party”
TOP FIVE II is a 200 foot Hakvoort from 2021, the newest boat in this countdown. She has a dedicated owner’s deck with its own dining area, and a Jacuzzi on the foredeck.
She sleeps 12 in six staterooms plus a media room that converts to a cabin, with 19 crew. The toys include 4 jet skis, 2 SeaBobs, an eFoil and an inflatable slide. She winters in the BVI, the USVI, the Leewards, the Windwards and the Bahamas, and stays in the Bahamas for summer. Rates run from $600,000 per week off-peak, up to $650,000 per week plus APA.
2. ATLANTIC
“A Replica of the 1903 Schooner”
ATLANTIC is a 212 foot three-masted schooner, built by Van der Graaf in 2010 as a replica of the 1903 schooner Atlantic, to a William Gardner design. She was refit in 2025, and she is the biggest sailing yacht in this countdown.
Inside there is a full-beam salon, a separate dining room and an observation room. She takes 12 guests in 6 en-suite cabins with 12 crew. Summers are in Sicily, Sardinia, Greece and the French Riviera, and winters in the Leewards, the Windwards, the BVI and Central America. Rates run from €150,000 per week off-peak, up to €200,000 per week plus 30% APA.
1. OKTO
“Built Around a Contraflow Pool”
OKTO is a 218 foot (66 meter) ISA motor yacht built in 2014, the biggest superyacht in this countdown. Her main deck aft is built around an infinity-edge contraflow swimming pool, and glass doors open it straight into the main salon.
She takes 11 guests in six suites, including a main-deck primary suite with a king bed and a retractable private balcony, and 16 crew. There is a gym, a massage room, a beauty salon and an elevator, and she carries 3 tenders, jet skis, SeaBobs, eFoils and an inflatable water park. She summers in Sicily, Sardinia, the Riviera and the Balearics, and winters in the Bahamas, the Leewards, the Windwards and the BVI. Rates run from €590,000 per week off-peak, up to €620,000 per week plus APA.
The 12 at a glance
The 12 at a glance, biggest first. Guest numbers are the most each listing describes, and rates are the lowest weekly rate on each listing, before expenses; a dash means the listing gives no crew number.
| # | Yacht | Length | Type | Guests | Crew | Weekly rate |
|---|---|---|---|---|---|---|
| 1 | OKTO | 218 ft | Motor | 11 | 16 | from €590,000 |
| 2 | ATLANTIC | 212 ft | Sail | 12 | 12 | from €150,000 |
| 3 | TOP FIVE II | 200 ft | Motor | 12 | 19 | from $600,000 |
| 4 | SOUTH | 180 ft | Motor | 12 | 14 | from $320,000 |
| 5 | YCM FIFTY | 165 ft | Motor | 14 | 9 | from €160,000 |
| 6 | SWEET CAROLINE II | 165 ft | Motor | 12 | – | from $199,000 |
| 7 | TCB | 164 ft | Motor | 12 | – | from $175,000 |
| 8 | NO BAD IDEAS | 160 ft | Motor | 12 | 9 | from $225,000 |
| 9 | ARABELLA | 157 ft | Sail | 40 | 6 | from $125,000 |
| 10 | HYPERION | 156 ft | Sail | 6 | 8 | from $112,000 |
| 11 | JUBILEE | 151 ft | Motor | 12 | 13 | from €180,000 |
| 12 | KEFI | 150 ft | Motor | 12 | 9 | from $175,000 |
The Mediterranean giants that cross for the winter
Most of the yachts below are bigger than anything in the countdown. They spend summer in the Mediterranean and winter in the Caribbean, and they are chartered through their own central agents rather than listed here. The details and rates come from their builders and the brokers who market them; rates are indicative and are confirmed at booking. Our brokers can check dates and book any of them: ask us about a winter charter. LUNA, the 115 meter Lloyd Werft, isn’t among them: she is privately owned and not offered for charter.
KISMET, 400 feet
KISMET is a 122 meter Lurssen delivered in 2024, with an exterior by Nuvolari Lenard and an interior by Reymond Langton. She has a hybrid powertrain that can run on electric power alone. She takes 12 guests in 9 cabins with 37 crew. Her winter season covers the BVI, St Barth, the Grenadines and the Bahamas, and rates start from €3,000,000 per week.
BREAKTHROUGH, 390 feet
BREAKTHROUGH is a 119 meter Feadship delivered in 2025, described as the first superyacht to run hydrogen fuel cells. She has an RWD exterior and a 19 meter beam, and takes 12 guests with 46 crew. She charters in the Mediterranean in summer and the Caribbean in winter, with rates from €3,500,000 per week.
AQUARIUS, 301 feet
AQUARIUS is a 92 meter Feadship from 2016, built for Steve Wynn and designed inside and out by Sinot. She has a 7 meter pool on the aft deck, a beach club and a helipad, and takes 12 guests in 6 cabins. She charters in the Mediterranean in summer and the Caribbean in winter, from $1,500,000 per week.
ROMEA, 268 feet
ROMEA is an 82 meter Abeking & Rasmussen from 2015, with exterior and interior by Terence Disdale. Her beach club has a spa, a massage room and a gym. She takes 12 guests in 6 cabins. Her summers are in the South of France, Naples, Sicily, Sardinia and Corsica, and her broker has announced Caribbean winter charters covering the Leewards, the Virgin Islands and the Windwards. Her rate is on request.
MALIA, 255 feet
MALIA is a 77.7 meter Golden Yachts from 2023, refit in 2024, and the builder’s first axe bow. She has a glass-edged infinity pool whose glass-bottom Jacuzzi lights the deck below, a pickleball court on the bow and a Seabreacher submersible watercraft. She takes 12 guests in 8 cabins with 22 crew, spends summer in the Mediterranean and takes Caribbean bookings in winter, from €750,000 per week.
QUANTUM OF SOLACE, 238 feet
QUANTUM OF SOLACE is a 72.6 meter Turquoise from 2012 with a 16 foot pool, a bar and a dining area on the sun deck. She takes 12 guests in 7 cabins. In winter she moves to the Caribbean, covering the Bahamas, the BVI, the USVI, the Leewards and the Windwards. Her winter 2026-27 rates run from $574,000 to $637,000 per week.
AXIOMA, 236 feet
AXIOMA is a 72 meter Dunya Yachts from 2013 with an Alberto Pinto interior, a double-height main salon and an 8 seat 3D cinema. She takes 12 guests in 6 cabins with 20 crew. She winters in the Caribbean and summers in the Mediterranean, and is often seen in France, Italy, Monaco and St Barts. Rates start from €525,000 per week in low season, and €580,000 per week in high season.
JOY, 230 feet
JOY is a 70 meter Feadship from 2016, with a Bannenberg & Rowell exterior, a Studio Indigo interior and air-conditioned outdoor spaces across five decks. She takes 12 guests with 19 crew. She summers in the Mediterranean and takes winter bookings in the Caribbean, from $650,000 per week in the Caribbean, against $700,000 per week in the Mediterranean.
VERTIGO, 220 feet
VERTIGO is a 67 meter Alloy Yachts sloop from 2011, designed by Philippe Briand and described as the largest sailing yacht built in the Southern Hemisphere. She had a major refit in 2018-19 and takes 12 guests with 11 crew. She sails the Mediterranean in summer and Bermuda and the Caribbean in winter, from €360,000 per week.
LADY BRITT, 207 feet
LADY BRITT is a 63 meter Feadship from 2011 with a Redman Whiteley Dixon interior, a spa and a Finnish sauna with direct access to the sea. She takes 12 guests in 7 cabins with 16 crew. She spends summers in the Mediterranean and winters in the Caribbean, from $465,000 per week.
Booking one of these for the winter
For the 12 boats in the countdown, each name links to the full listing with photos, cabin plans and rates. For the Mediterranean yachts, or if your dates or group size don’t fit any of them, tell us your dates and group size and a broker will come back with what is free. If you are after something smaller, see our top 10 superyachts for the BVI.
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